This invention relates to organic electroluminescent (EL) devices comprising a light-emitting layer containing a host and a dopant where the dopant comprises a boron compound complexed by two ring nitrogens of a deprotonated bis(azinyl)amine ligand.
While organic electroluminescent (EL) devices have been known for over two decades, their performance limitations have represented a barrier to many desirable applications. In simplest form, an organic EL device is comprised of an anode for hole injection, a cathode for electron injection, and an organic medium sandwiched between these electrodes to support charge recombination that yields emission of light. These devices are also commonly referred to as organic light-emitting diodes, or OLEDs. Representative of earlier organic EL devices are Gurnee et al. U.S. Pat. No. 3,172,862, issued Mar. 9, 1965; Gurnee U.S. Pat. No. 3,173,050, issued Mar. 9, 1965, Dresner, xe2x80x9cDouble Injection Electroluminescence in Anthracenexe2x80x9d, RCA Review, Vol. 30, pp. 322-334, 1969, and Dresner U.S. Pat. No. 3,710,167, issued Jan. 9, 1973. The organic layers in these devices, usually composed of a polycyclic aromatic hydrocarbon, were very thick (much greater than 1 xcexcm). Consequently, operating voltages were very high, often  greater than 100V.
More recent organic EL devices include an organic EL element consisting of extremely thin layers (e.g.  less than 1.0 xcexcm ) between the anode and the cathode. Herein, the organic EL element encompasses the layers between the anode and cathode electrodes. Reducing the thickness lowered the resistance of the organic layer and has enabled devices that operate at much lower voltage. In a basic two-layer EL device structure, described first in U.S. Pat. No. 4,356,429, one organic layer of the EL element adjacent to the anode is specifically chosen to transport holes, therefore, it is referred to as the hole-transporting layer, and the other organic layer is specifically chosen to transport electrons, referred to as the electron-transporting layer. The interface between the two layers provides an efficient site for the recombination of the injected hole/electron pair and the resultant electroluminescence.
There have also been proposed three-layer organic EL devices that contain an organic light-emitting layer (LEL) between the hole-transporting layer and electron-transporting layer, such as that disclosed by Tang et al [J. Applied Physics, Vol. 65, Pages 3610-3616, 1989]. The light-emitting layer commonly consists of a host material doped with a guest materialxe2x80x94dopant, which results in an efficiency improvement and allows color tuning.
Since these early inventions, further improvements in device materials have resulted in improved performance in attributes such as color, stability, luminance efficiency and manufacturability, e.g., as disclosed in U.S. Pat. No. 5,061,569, U.S. Pat. No. 5,409,783, U.S. Pat. No. 5,554,450, U.S. Pat. No. 5,593,788, U.S. Pat. No. 5,683,823, U.S. Pat. No. 5,908,581, U.S. Pat. No. 5,928,802, U.S. Pat. No. 6,020,078, and U.S. Pat. No. 6,208,077, amongst others.
Notwithstanding these developments, there are continuing needs for organic EL device components, such as dopants, that will provide high luminance efficiencies combined with high color purity and long lifetimes.
A useful class of dopants is derived from the 5,6,5-tricyclic pyrromethene-BF2 complexes and disclosed in U.S. Pat. No. 5,683,823; JP 09,289,081A; and JP 11,097,180A. These materials are characterized by typically narrow emission spectra, which may result in attractively high color purity. However, with the 5,6,5-tricyclic pyrromethene-BF2 system the shortest known wavelength of emitted light is green. Furthermore, the green electroluminescence generated from the 5,6,5-tricyclyc pyrromethene-BF2 is relatively inefficient. In order to achieve highly efficient OLEDs, one can attempt to use fused phenyl rings as substituents thereby extending conjugated xcfx80-system. As a result, however, the emission wavelength is red-shifted yielding a reddish-amber color, which is the shortest wavelength that can be emitted by 5,6,5-tricyclic pyrromethene-BF2 complexes with good efficiency. Introduction of substituents has not led to efficient green or blue emitters. For example, the introduction of N at the bridging position in the 5,6,5-tricyclic boron complexes ([N-(2H-pyrro-2-ylidene-xcexaN)-1H-pyrrol-2-aminato-xcexaN1]difluoroboron complexes) leads to an even further red-shift as reported by Sathyamoorthi et al. [Heteroatom Chem. Vol. 4 (6), Pages 603-608, 1993]. Thus, these nitrogen-bridged 5,6,5-tricyclic systems have not been used in OLED devices. It is not feasible that a blue emitter may be derived from any 5,6,5-tricyclic boron system.
It is a problem to be solved to provide a complexed-boron light-emitting dopant for the light-emitting layer of an OLED device that emits in the blue range and exhibits desirable luminance efficiency.
The invention provides an OLED device comprising a light-emitting layer containing a host and a dopant where the dopant comprises a boron compound complexed by two ring nitrogens of a deprotonated bis(azinyl)amine ligand. The invention also provides compounds and an imaging device containing the OLED device.